Ammonium Chloride → 4-Bromo-beta,beta-dimethylbenzeneethanol
反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([O-])=[O:10])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:13])([CH3:12])[CH2:9][OH:10])=[CH:6][CH:7]=1参加物
5
実験手順
To a solution of 2-(4-bromophenyl)-2-methylpropanoate (8.9 g, 33 mmol) in THF (100 mL) under nitrogen was added LiAlH4 (1.6 g, 43 mmol) in portions at 0° C. The resulting solution was stirred at 0° C. for 1 hour before the addition of saturated aqueous NH4Cl (50 mL). The mixture was then extracted with EtOAc (3×80 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by MPLC on Silica gel with 2-5% EtOAc/hexane to afford 2-(4-bromophenyl)-2-methylpropan-1-ol as a colorless oil. MS ESI: [M+H]+ m/z 229, 231; 1H NMR (400 MHz, CDCl3) δ 7.47 (d, J=6.8 Hz, 2H), 7.28 (d, J=6.8 Hz, 2H), 3.61 (s, 2H), 1.58 (s, 6H).